Search Deals on
Housatonic Vacation Packages

Build your package with 2 more options

Housatonic Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $586, price is now $455 per person
$455
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

3 out of 5
Save 100% on your flight
Price was $13,702, price is now $9,284 per person
$9,284
per person
May 21 - May 25
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Book a stay at this family-friendly cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.
Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

3 out of 5
Save 100% on your flight
Price was $13,397, price is now $9,315 per person
$9,315
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Book a stay at this family-friendly cottage in Hunter. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.
Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

3 out of 5
Save 100% on your flight
Price was $11,239, price is now $8,269 per person
$8,269
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Stay at this cottage in Tannersville. Enjoy free parking, a pool table, and balconies. Popular attractions Hunter Mountain and Mountain Trails Cross Country Ski and Snowshoe Center are located nearby.
Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $2,435, price is now $1,838 per person
$1,838
per person
May 21 - May 25
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Book a stay at this business-friendly cottage in Windham. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Save 100% on your flight
Price was $930, price is now $723 per person
$723
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
Price was $718, price is now $563 per person
$563
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Stay at this hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hunter Mountain and H Ski Lift are located nearby.
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

2 out of 5
Price was $607, price is now $484 per person
$484
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Stay at this hotel in Hunter. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the helpful staff in our reviews. Popular attractions Hunter Mountain and D Ski Lift are located nearby.

Housatonic Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $2,435, price is now $1,838 per person
$1,838
per person
May 21 - May 25
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

3 out of 5
Save 100% on your flight
Price was $13,702, price is now $9,284 per person
$9,284
per person
May 21 - May 25
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to Hudson (HCC)
Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

3 out of 5
Save 100% on your flight
Price was $13,397, price is now $9,315 per person
$9,315
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)
Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

3 out of 5
Save 100% on your flight
Price was $11,239, price is now $8,269 per person
$8,269
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Hudson (HCC)